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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:57:10 UTC

Update Date

2021-09-24 03:57:10 UTC

HMDB ID

HMDB0303700

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Feruloyltartaric acid

Description

Feruloyltartaric acid, also known as trans-fertaric acid or feruloyltartarate, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Feruloyltartaric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Feruloyltartaric acid can be found in common grape, grape wine, sherry, and vinegar, which makes feruloyltartaric acid a potential biomarker for the consumption of these food products.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0303700
     RDKit          3D
Feruloyltartaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.5194    1.2523    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    0.1522   -0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3272   -0.4915   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -0.0826   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235   -0.7340   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5979   -0.3483   -0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    0.6396    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998    0.9852    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951    1.9404    1.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    0.2657    0.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    0.6263    0.7375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2579    0.9462   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.7954   -1.6117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    1.4363   -0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161   -0.5280    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9852   -0.6988    2.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762   -0.1270    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    0.1845    3.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3745   -0.0811    1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -1.8041   -1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874   -2.2125   -2.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -1.5651   -2.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972   -1.9451   -2.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6711    1.9312   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    0.8395    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    1.7995   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    0.7552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574   -0.9101   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674    1.2295    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751    1.4893    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034    2.4032   -0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -1.4733    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433   -1.0486    3.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0061   -0.8694    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -2.3084   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -3.0639   -3.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -1.4662   -2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  1
 14 31  1  0
 15 32  1  6
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END


  Mrv0541 02241216122D          

 23 23  0  0  0  0            999 V2000
    1.9065    3.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    3.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    1.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    2.8370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.0120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4775    1.5995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4775    0.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -4.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -3.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -3.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -0.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    0.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    1.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 21  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 23  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303700

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@H]([C@@H](O)C(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m1/s1

> <INCHI_KEY>
XIWXUSFCUBAMFH-WEPHUFDCSA-N

> <FORMULA>
C14H14O9

> <MOLECULAR_WEIGHT>
326.2556

> <EXACT_MASS>
326.063782046

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.889335399205578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.7438542420000003

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.47823248663642

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.951276504214371

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
74.22519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303700
     RDKit          3D
Feruloyltartaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.5194    1.2523    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    0.1522   -0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3272   -0.4915   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -0.0826   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235   -0.7340   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5979   -0.3483   -0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    0.6396    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998    0.9852    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951    1.9404    1.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    0.2657    0.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    0.6263    0.7375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2579    0.9462   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.7954   -1.6117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    1.4363   -0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161   -0.5280    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9852   -0.6988    2.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762   -0.1270    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    0.1845    3.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3745   -0.0811    1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -1.8041   -1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874   -2.2125   -2.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -1.5651   -2.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972   -1.9451   -2.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6711    1.9312   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    0.8395    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    1.7995   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    0.7552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574   -0.9101   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674    1.2295    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751    1.4893    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034    2.4032   -0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -1.4733    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433   -1.0486    3.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0061   -0.8694    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -2.3084   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -3.0639   -3.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -1.4662   -2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  1
 14 31  1  0
 15 32  1  6
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.559   6.066   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.225   5.296   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.891   6.066   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.776   2.986   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.442   3.756   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.442   5.296   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.225   3.756   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.891   2.986   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.891   1.446   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.776  -7.794   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.776  -6.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.110  -5.484   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.110  -3.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.776  -3.174   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.442  -3.944   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.442  -5.484   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.891  -6.254   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.225  -5.484   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.776  -1.634   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.442  -0.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.442   0.676   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.776   1.446   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.559   2.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7    2    8   23                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8   21                                                       
CONECT   10   11                                                            
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21    9   20   22                                                  
CONECT   22   21                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0303700
HETATM    1  C1  UNL     1       5.519   1.252   0.067  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.493   0.152  -0.812  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.327  -0.492  -1.171  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.083  -0.083  -0.679  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.923  -0.734  -1.045  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.598  -0.348  -0.562  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.350   0.640   0.263  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.000   0.985   0.716  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.195   1.940   1.509  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.079   0.266   0.278  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.401   0.626   0.738  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.258   0.946  -0.401  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.873   0.795  -1.612  1.00  0.00           O  
HETATM   14  O5  UNL     1      -5.538   1.436  -0.265  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.916  -0.528   1.602  1.00  0.00           C  
HETATM   16  O6  UNL     1      -2.985  -0.699   2.663  1.00  0.00           O  
HETATM   17  C11 UNL     1      -5.176  -0.127   2.244  1.00  0.00           C  
HETATM   18  O7  UNL     1      -5.198   0.185   3.479  1.00  0.00           O  
HETATM   19  O8  UNL     1      -6.374  -0.081   1.526  1.00  0.00           O  
HETATM   20  C12 UNL     1       2.067  -1.804  -1.918  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.287  -2.213  -2.407  1.00  0.00           C  
HETATM   22  C14 UNL     1       4.443  -1.565  -2.044  1.00  0.00           C  
HETATM   23  O9  UNL     1       5.697  -1.945  -2.514  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.671   1.931  -0.004  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.540   0.839   1.119  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.498   1.799  -0.023  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.016   0.755   0.000  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.257  -0.910  -0.901  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.167   1.230   0.631  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.275   1.489   1.404  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.803   2.403  -0.361  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.963  -1.473   1.070  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.443  -1.049   3.462  1.00  0.00           H  
HETATM   34  H11 UNL     1      -7.006  -0.869   1.486  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.154  -2.308  -2.200  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.360  -3.064  -3.095  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.545  -1.466  -2.247  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   30
CONECT   12   13   13   14
CONECT   14   31
CONECT   15   16   17   32
CONECT   16   33
CONECT   17   18   18   19
CONECT   19   34
CONECT   20   21   35
CONECT   21   22   22   36
CONECT   22   23
CONECT   23   37
END

HMDB0303700
     RDKit          3D
Feruloyltartaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.5194    1.2523    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    0.1522   -0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3272   -0.4915   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -0.0826   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235   -0.7340   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5979   -0.3483   -0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    0.6396    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998    0.9852    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951    1.9404    1.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    0.2657    0.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    0.6263    0.7375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2579    0.9462   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.7954   -1.6117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    1.4363   -0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161   -0.5280    1.6021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9852   -0.6988    2.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762   -0.1270    2.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    0.1845    3.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3745   -0.0811    1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -1.8041   -1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874   -2.2125   -2.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -1.5651   -2.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972   -1.9451   -2.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6711    1.9312   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5401    0.8395    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    1.7995   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    0.7552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574   -0.9101   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674    1.2295    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751    1.4893    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034    2.4032   -0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -1.4733    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433   -1.0486    3.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0061   -0.8694    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -2.3084   -2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -3.0639   -3.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -1.4662   -2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  1
 14 31  1  0
 15 32  1  6
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
trans-Fertaric acid	ChEBI
trans-Fertarate	Generator
(2R,3R)-trans-Fertarate	Generator
Feruloyltartarate	Generator

Chemical Formula

C₁₄H₁₄O₉

Average Molecular Weight

326.2556

Monoisotopic Molecular Weight

326.063782046

IUPAC Name

(2R,3R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

(2R,3R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@H]([C@@H](O)C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m1/s1

InChI Key

XIWXUSFCUBAMFH-WEPHUFDCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Fatty acid ester
Sugar acid
Phenol
Alpha-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:76116 )
phenols (CHEBI:76116 )
cinnamate ester (CHEBI:76116 )
dicarboxylic acid (CHEBI:76116 )
tetraric acid derivative (CHEBI:76116 )

Ontology

Not Available

White wine (FooDB: FOOD00917)
Grape wine (FooDB: FOOD00612)

Fortified wines

Sherry (FooDB: FOOD00632)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.36	ALOGPS
logP	0.74	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	74.23 m³·mol⁻¹	ChemAxon
Polarizability	29.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	173.007	32859911
AllCCS	[M+H-H2O]+	169.982	32859911
AllCCS	[M+Na]+	176.606	32859911
AllCCS	[M+NH4]+	175.804	32859911
AllCCS	[M-H]-	170.474	32859911
AllCCS	[M+Na-2H]-	170.511	32859911
AllCCS	[M+HCOO]-	170.678	32859911
DeepCCS	[M+H]+	179.894	30932474
DeepCCS	[M-H]-	177.536	30932474
DeepCCS	[M-2H]-	210.84	30932474
DeepCCS	[M+Na]+	186.07	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 10V, Positive-QTOF	splash10-056r-0936000000-df45e31840694c1d2b1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 20V, Positive-QTOF	splash10-004i-2931000000-d1a77c0c3104784ff180	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 40V, Positive-QTOF	splash10-005i-3900000000-663c5138128638f1738e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 10V, Negative-QTOF	splash10-0059-3983000000-a2c5acc144c780e75984	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 20V, Negative-QTOF	splash10-005l-3950000000-9b4cc92a910ad49e86d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 40V, Negative-QTOF	splash10-004i-3920000000-48689ca2a662e37793bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 10V, Positive-QTOF	splash10-004i-0893000000-37f54e20b67b4d1b6ec0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 20V, Positive-QTOF	splash10-01ot-0900000000-35df6126ac0db387ec9b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 40V, Positive-QTOF	splash10-0002-1900000000-5604fc8eac6de087b79d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 10V, Negative-QTOF	splash10-0019-9450000000-b412994c49046210599b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 20V, Negative-QTOF	splash10-000i-7930000000-ac327a6312e7912b2e65	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyltartaric acid 40V, Negative-QTOF	splash10-000t-2910000000-b21995fb963f97f0b8a1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018773

KNApSAcK ID

C00055851

Chemspider ID

30785799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72551457

PDB ID

Not Available

ChEBI ID

76116

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Feruloyltartaric acid (HMDB0303700)

MOL for HMDB0303700 (Feruloyltartaric acid)

3D MOL for HMDB0303700 (Feruloyltartaric acid)

3D SDF for HMDB0303700 (Feruloyltartaric acid)

3D-SDF for HMDB0303700 (Feruloyltartaric acid)

PDB for HMDB0303700 (Feruloyltartaric acid)

3D PDB for HMDB0303700 (Feruloyltartaric acid)

SMILES for HMDB0303700 (Feruloyltartaric acid)

INCHI for HMDB0303700 (Feruloyltartaric acid)

Structure for HMDB0303700 (Feruloyltartaric acid)

3D Structure for HMDB0303700 (Feruloyltartaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra